Cuba Trip Day 1: Arrival in Havana

Two things that were unique about our departure to Havana: (1) they strongly recommend that you wrap your luggage in saran wrap to prevent theft (at a cost of $15), and (2) everything in Cuba is so expensive that you are sure to have a few passengers bringing back giant stuffed animals. Not small stuffed animals, GIANT stuffed animals. We arrived safely and proceeded to Cuban customs. It may have just been the day we were there, but the employees at the airport were all very, very attractive. Male and female. The females wear fishnet stockings. I’m not kidding. We passed through customs and headed to our hotel: the Hotel Nacional. It is a beautiful hotel, rich in history. Sadly, while the hotel is one of the nicest on the island (if not the nicest), it would be comparable to a Courtyard Marriott in the U.S. in terms of amenities. The hotel has beautiful ocean views, decent restaurants, a solid cigar shop (Casa de Habanos), and then the patio which is great. In the end, we spent very little time at the hotel anyway, so it was certainly pleasant for our purposes.

Before we even checked in, I walked out to the patio. Immediately, I was reminded of the blog post I wrote last summer about a vacation to Scotland. I wrote that teeing off on the New Course at St. Andrews felt like a religious experience; here in Havana, a few steps into the back patio area, I felt a similar pit in my stomach at just the thought of enjoying a Cuban cigar…in Havana…at the Hotel Nacional. Little did I know, I would be doing it about a half dozen times over the course of 6 days.

Hotel Nacional from the Ocean

We had a great lunch, walked around Havana, stopped into a tobacconist where I picked up a few cigars, and then headed back to the hotel to relax. I smoked a Partagas D Series #4.

Dinner was at a “paladar”, which is a private Cuban home that serves as a restaurant. Most of our lunches on the trip were at government-run restaurants, and most were fine. By far, though, the best meals were the dinners at different paladars.

Outside the Paladar of our first dinner

After dinner, our group returned to the hotel, and most of us enjoyed cigars on the lawn with live, Cuban music in the background. I had a Montecristo #2. I thought two cigars in a day might be overkill, but little did I know that by the halfway point of the trip, I would realize there were too many great cigars to smoke and not enough time. Something would have to give…




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Wingtip Founder & CEO, Ami Arad is the quintessential modern gentleman. He has distinctive taste, an eclectic style, and dresses for every occasion. Ami developed his vision for Wingtip at a young age; even back in high school where four years of speech and debate meant weekends wearing a coat and tie, he was in his element. Years of working in upscale men’s clothing stores and socializing in cigar shops, coupled with his entrepreneurial spirit, inspired Ami to develop Wingtip, a men’s specialty store and private social club.